Playing for Keeps
by Annaleise Marie
Summary: [crime!AU] Dean is a professional kidnapper, snatching up the spoiled kids of rich fat cats and ransoming them for obscene amounts of money. It's not honest, but hey, he's gotta put Sammy through school somehow and ivy ain't cheap. When he kidnaps Castiel, the 20-year-old son of a publishing mogul, Dean figures it'll be a pretty cut-and-dry job. Dean is so wrong. [prompt fill]
1. Part One

**Playing for Keeps**  
Annaleise Marie  
_cross-posted from livejournal  
__username: girlgotagun_

**Pairing(s)**: Dean/Cas  
**Full List of Kinks**: kidnapping/abduction, hurt/comfort, anal, oral, fingering, first time, angst, masturbation, schmoop/waff  
**WARNING**: retrospective discussions of (non-sexual) child abuse/death of a child

Originally written for a prompt on the spnkink-meme livejournal community.

**Part One**

X

There weren't really any nice-sounding words to describe Dean Winchester's profession. The best he could come up with, when asked by people in bars or on the rare blind dates he let his brother set him up on—Sammy had been on a kick about Dean settling down ever since he found Jess—was that he brokered high-asset deals with some of the major players in the pacific mid- and northwest. But even that was a bit of a stretch and, despite what may be expected, Dean didn't like to make it a habit of lying. Lying betrayed guilt, and guilt drew attention. Attention that Dean couldn't afford to have on him.

So he started just saying that he worked in sales. Which was true enough, he supposed. So what if he was selling something _back_ to a person? So what if he had stolen it in the first place?

Okay, so it wasn't really called _stealing_ in this particular case. Police called it kidnapping. The feds could probably push for a human trafficking charge, if they wanted to. Words like _hostage_ and _captive_ and _victim_ could be thrown around. _Ransom_. _Abduction_.

So see, there were no really pretty words for it. And maybe what Dean did wasn't pretty; wasn't shiny and glamorous and strictly above board, the way Sammy wanted to live, wanted him to live. But it got the job done. The children of major players—corporate fat cats and low-level politicians—were easy targets, and their parents were pretty used to tossing money at a problem rather than addressing it themselves, so the cash that Dean requested in exchange for returning them was pretty easily handed over. The kids were always returned, safe and sound, and Dean figured it was pretty much a no-harm no-foul sort of situation.

He had done this six times. Well five really, if you were counting the times that he had actually planned and executed the whole thing. The first time, when he was twenty-one, was a bit of a fluke. Dean had been waiting for Sam to get out of school, leaning against the Impala across the street from the school. He had been waiting about five minutes when he heard a kid crying. After a bit of investigation he found her, crouched under the slide in the park behind him. The girl was a mess, covered in what looked like days worth of dirt and grime, leaves and twigs stuck in her matted blonde hair, startlingly clean streaks across her face where her tears were trailing down and her nose was running.

Dean hadn't really thought twice about it. When she had been too distressed to pull herself together long enough to tell him her name, address, phone number, or even her parents names, Dean had taken her to the police station. It turned out that her name was Emma, she was six years old, and she had been missing for just under a day—no matter what the layers of dirt said to the contrary.

It turned out that her parents had offered a reward for her safe return. So after Dean was questioned thoroughly to make sure that he hadn't snatched her up as she walked the short distance from her bus stop to her house or something, he was tearfully given a check for five thousand dollars from her grateful parents.

By the time he got back to the school to finally collect Sam, his brother was livid. Until, that is, two days later when his early acceptance to Stanford University arrived. The little nerd had been offered a full ride for his tuition, but nothing to break the cost of books, room and board, meal plans, lab fees, and the million other things that apparently came along with a very expensive piece of paper. Their dad had told Sam straight-up that he wouldn't be paying for any of that. Sam and Dean were expected to stay in North Dakota and help him and Bobby around the shop. Dean was cool with that, but he knew that Sam never had been.

He spent the next week on the phone with the university, and every penny of that five thousand went to Sam's dorm and meals for his first semester. He figured it up and worked out how to pay for the lab fees and books out of his wages at the garage. The hardest part was convincing the university snobs to keep his name out of their mouths, to let Sam think that he had received some grant or scholarship that had covered the costs. He knew Sam would never take it, would stubbornly work his ass off full-time to barely make ends meet and sacrifice his school work to not have to accept help after the things that their dad said, and Dean would be damned if he was going to let his little brother rip their family apart to pursue his dreams and then _fail_.

The next semester he actually got his friend Charlie to set up a bogus grant and submit it to Stanford for Sam. Because where the second wave of money came from…Sammy _definitely_ couldn't ever find out about that.

Turned out that if people would pay a lot as a reward for their kid's return, it was _nothing_ compared to what they'd pay in ransom. The first time he did it, he aimed high—the twelve-year-old daughter of some Hollywood big shot. He'd planned the job for months, learning not only the routines of the girl—piano practice, tutoring, ballet, middle school lacrosse—but also everyone around her; parents (rarely), nanny (often), driver and household staff (intermittent), until finally he spotted a consistent spot in the routine where the girl was alone.

She walked twice a week from her tutor's house to the ballet studio four blocks away. Dean had followed, pulling up beside her. The lie slid out easily—alarmingly so, really, considering how much Dean hated to lie—as he told her that her father had sent him to pick her up, that there had been an unexpected change in the schedule and that he couldn't come to get her himself, that the driver and car she was used to was currently being used by her mother.

It made him a little sad how easily she believed him, how unsurprised she seemed as she got in the car.

Dean had taken her to Charlie's place, let his friend distract her with video games and a bunch of geek stuff that he never really cared to understand, and within a day the ransom he demanded was transferred into the bogus account that Charlie had set up. As Charlie quickly filtered the money through a couple dozen of others, typing feverishly as she buried the paper trail between each, Dean had returned the girl to where he had picked her up.

He had never really tried to scare the girl, but he had also been careful to make sure that her descriptions of him, of Charlie, of the house would be too general to really pin either of them down. He had also taken extra care not to touch her or any of her belongings, careful not to leave behind fingerprints or DNA. Not that the police would have anything to compare them to. Dean had never been taken in for anything, had no prints or DNA on file.

The whole thing had gone shockingly smoothly. Half a million dollars was split and distributed. Charlie's take amounted to her rent and living expenses for a year, plus her mom's healthcare expenses—the woman had been in a coma since Charlie was a kid, and after Charlie got into trouble as a teenager she couldn't work legitimately, so the situation was a win/win for her. He deposited enough into the fake grants to carry Sam through school for another year, and the rest went into a savings account.

That should've been the end of it.

But it's a basic law of finances and the driving force of the economy that the more money you have, the more you spend. And by the end of Sam's sophomore year, Dean found himself planning again.

And so it continued. By the time Sam was set to graduate, Dean had completed his fifth ransom exchange. No one ever got hurt, and the only financial hit was to people who had way more money than sense—the type of people who dropped a few million dollars on a penthouse apartment in LA. So Dean still figured no harm, no foul. Apply all the nasty words to it that you want.

And then Sam had called him; told him that he had scored well enough on his LSATs to basically take his pick of law schools. So Dean began planning one more heist. The target this time was the twenty-year-old son of a major publishing tycoon, Castiel Novak.

X

The day that changed Castiel's life had started like any other—well, maybe not _any_ other. Most other days, he'd be in Ithaca, New York. He was about to start his junior year of undergrad at Cornell University. Cornell was his father's college. Castiel was an English Journalism major. That was his father's major. And it made sense, see, that his school and his area of study would be his father's, because Castiel was being groomed to become his father.

He'd sooner die.

So maybe that day didn't start exactly like any other. Castiel was home for the summer, working at his father's publishing house in Seattle, Washington. Long hours, no thanks, and a guaranteed trip at the end of the day back to his childhood home, where he would lock his bedroom door and be very quiet, pretending he didn't exist, and hope that it was one of those nights where his father forgot that his youngest son wasn't still all the way across the country.

But it was like any other summer day, and that was the point. That was what had finally driven Castiel nearly out of his skin, had sent him surging out the doors of the airless corporate skyrise when his lunch hour hit, had sent him nearly barreling into the streets, nearly right in front of a big black muscle car. The car slammed on its breaks and the driver stuck his head out. The guy was young—maybe late twenties—with short blonde hair and green eyes vivid enough to contend with Castiel's own bright blue.

The driver's plump lips parted in surprise. "You trying to get yourself killed, kid?"

Castiel nearly laughed. The endless hours, the never good enough, the scorched smell of hot paper and binding glue, the belt and the sharp smell of gin, they all rolled through his head. He didn't know what made him say it, other than the fact that it may be the truth. "Maybe."

The guy blinked at him, looking confused. Like he wasn't sure about the turn his day had taken. Like he was about to do something crazy. "Get in."

"What?" Castiel blinked at him in surprise.

The man laughed. "Seriously, get in." He jerked his head at the passenger side door.

And Castiel didn't know what made him do it, other than the fact that the car looked like it could get him far, far away from his current situation, and there was nothing that the guy could do to him that would be worse than what he was running from.

Castiel got in the car.

X

Dean couldn't believe it. He had been tailing Castiel—Cas, he decided; Castiel was too much on the tongue—for a week now. He had figured the job would be trickier than the others over the years. Cas was an adult, twenty years old, and would know better than to just get in a car with a stranger.

But then Dean had nearly run him over as the little guy went barreling out of the publishing house offices and into the street, his eyes wild and desperate, the haunted look of _too much and crashing down_ radiating out of deep blue. And Dean had offered him a way out, and Cas had taken it.

He couldn't believe it. The job that was supposed to take at least a month to plan was suddenly in motion. And fuck, that gamble was going to cost him. Because he wasn't ready. Charlie was still in California, waiting for her part in the plan to come up to Washington.

See, because Cas was twenty and _really_ should have known better, Dean had figured this job was going to require a bit more nuance. The tentative plan was for him to learn Cas's routine and then shadow it; conveniently be wherever the young man was. Meet him, befriend him in that casual two young guys on vacation type of way. Invite him out with him and his good—single—friend Charlie. Spike his drink, take him back to their place, and then keep him that way all safe and quiet until the exchange was complete and he could be returned, happy as a clam, near enough to his own home to get there safely without Dean being spotted.

It was perfect. Clean, efficient, low-risk. The drugs would've even taken enough of the kid's memory to ensure that he couldn't reliably identify Dean.

So what did he do now? What did he do when the whole plan fell apart and Cas was sitting in the passenger's seat looking for all the world like he had just escaped the jaws of a man-eating monster?

He took a deep breath and started to talk. "Look, Cas, I don't know what was going on back there—"

"Cas?" The man asked, his eyes narrowing at Dean as though his mind were trying to work something out.

Dean laughed. "Yeah, well, Castiel is a bit of a mouthful."

There was a heavy pause. "Yeah, but…how do you know my name at all?"

_Shit_.

X

With the soaring suspicion, Castiel's heartbeat increased ten-fold, panic quickly setting in. He glanced down, his stomach dropping when he realized he had, as he thought, remembered to remove his employee ID badge before leaving the building. So how had the man known his name? He was a Novak, sure, and the Novaks were, as his father liked to remind him, _very important people_, but Castiel himself wasn't important. He hadn't done anything to be known for; his name had never been in print. He was the unknown factor. Well, mostly. His existence wasn't _secret_. It was more like no one had any reason to know about him.

Unless they had purposefully sought him out.

Unless they had made it their business to know about him.

"Are you…are you stalking me?" Castiel asked. "Is this one of those crazy obsession type of things? Oh my god, you're going to kill me aren't you? You're going to kill me and then keep my body around for days for all sorts of sick shit aren't you?"

The man gaped at him, looking genuinely horrified. "What? Where do you even get that shit? You think I'm Billy the Kid or something, Clarice?"

"Buffalo Bill."

"Whatever, Cas!" The man looked like he had never heard anything more ridiculous in his life. "The point is, _no_, I'm not stalking you. Well, okay. Maybe I was stalking you a bit, but not to kill you and snatch your skin or some shit and not because you're so fucking fantastic that I'm obsessed with you!"

"Why are _you_ acting all offended? I'm the one who's going to die!" Castiel felt like he couldn't breathe; there wasn't enough air in the car. His breath was coming in short, quick puffs that did nothing to expand his lungs, to deliver the oxygen his brain desperately needed. _Oh god, he was going to die._

"Would you stop saying that? You're not going to die! No one's ever died." The man pulled over suddenly and reached into the backseat to produce a crumpled paper bag. He checked inside, verifying that it was empty, and then pressed it over Castiel's mouth and nose, holding the younger man's head in place. "Shit, man, would you just calm down? You're going to be fine, alright?"

Castiel tried to focus on his breathing, tried to push away the panic that was squeezing his lungs painfully. But why? So that he wouldn't die? This nutbar was clearly going to kill him anyway. His nanny, Anna, had been right when he was a kid. Never get into cars with strangers. What had he been thinking?

"Listen." The man was speaking again as Castiel's breathing began to even out and oxygen started to flood his brain. "I'm really not gonna kill you, alright? I'm gonna level with you—you're being kidnapped. But I don't plan on hurting you; I've never hurt anyone. I'm going to ransom you, your father's going to pay it, and then you'll be returned safe and sound. Immediately. Alright? And as long as you keep your mouth shut and don't tell them it was me, you'll never have any reason to see me again. I swear it. Nothing has ever happened to anyone during one of my jobs."

Castiel nearly laughed. Of course the guy had done this before. Of-fucking-course. And what if he wasn't telling the truth? How many times could someone do this before someone got hurt? Surely someone had been hurt—killed—to keep him from getting turned in, right?

But he figured his best bet was to keep quiet until he figured out another plan, and he nodded, pulling the bag from his face. The car was in motion again, calmly winding its way through the streets of Seattle.

And it was a testament to how bad his life had really gotten, in tiny little ways over the years, that one of the greatest thoughts raging in Castiel's mind at that moment was that, tonight at least, he wouldn't be going back to his father's house.


	2. Part Two

**Playing for Keeps**  
Annaleise Marie  
_cross-posted from livejournal  
__username: girlgotagun_

**Part Two**

X

The car pulled to a stop outside of a—surprisingly nice, Castiel thought—apartment building. But then, he supposed that the kidnapping industry must be a fairly lucrative one, and people would be less likely to suspect a man who appeared to be well-off of such shady practices.

The man turned to him as he turned off the car. "Okay. We're going to go inside. You're going to walk with me calmly. Don't speak to anyone; don't even make eye contact with anyone. Don't try to run." There was a vague threat undercutting the instructions.

Castiel eyed the man suspiciously, sure he had caught him in another lie. "I thought you said you weren't planning on hurting me? That you hadn't hurt anyone?"

His questions didn't appear to unnerve the man. He just smirked back at Castiel. "I've never hurt anyone because no one's ever tested me before. You want to be the first?"

Castiel shook his head. The man seemed satisfied with the answer and shifted to get out of the car. Castiel's eyes widened when the man's jacket lifted slightly with the movement and he saw the pearl grip of a gun sticking out of his waistband. He tried to stay calm, to not start hyperventilating again. He needed to stay calm; needed to walk into the building like nothing was wrong—the guy said he would be safe if he did that, and maybe it was a lie, but it was better than the promise of harm if he didn't do as he was told.

He got out of the car as well and followed the man into the building. They crossed the lobby, the man nodding in a distracted way to the doorman, and then stepped onto an elevator. Castiel glanced at the buttons. There were fifteen floors, and the man pressed the button for number eight. Not the top floor, so the building likely was chosen as a cover, not his main residence, but not the ground floor—expensive, but ensured that passersby wouldn't happen to glance in his living room window. No chance of anyone spotting Castiel and reporting his whereabouts. The guy was smart.

Assuming, he thought, if all of his assumptions were correct. Who knew, maybe the man _did_ live here, came from an upper-class background and had the resources to go with it and was just the kind of psycho who did things like this.

"Do you actually live here?" he asked, trying for a casual, off-hand tone.

The man eyed him out of the corner of his eyes and cleared his throat. "Cas, you should probably just assume that I'm not planning on answering any questions you ask about me and my life."

"Why didn't you cover your face?"

The man sighed. "Fucking Christ."

There was a cheerful little _ding_ and then the doors slid open on the eighth floor. The man motioned for Castiel to step out first and then he followed, signaling for the younger man to head down the right side of the hall. They stopped in front of apartment 820, and the man turned the key quickly and ushered Castiel inside. Once there, he locked it back, along with no less than three deadbolts and—Castiel's heart sank—a padlock. The key to the padlock was on a chain around the man's neck, and he dropped the chain under the neck of his shirt once he was done with it, keeping it out of sight.

"Make yourself at home," the man said as he stepped around Castiel and headed for the kitchen.

The invitation surprised the younger man. "What? You're not going to keep me handcuffed to a bed or something?"

The man froze for a beat before turning back to look at him, a sly grin on his face. "I mean, I could if that's what you're into. But no, I was planning on letting you at least move around the apartment. As long as you don't do anything stupid."

Castiel turned this over in his head as he followed the man to the kitchen. "You don't seem like your average psycho killer."

The man snorted as he opened the fridge and pulled out a beer. "Probably because, like I've told you, I'm not a psycho killer." He untwisted the cap and tossed it into the trashcan before taking a drink, his eyes never leaving Castiel's.

The younger man looked away, feeling off-balance. Psycho killer he could deal with—maybe not _well_; how well could anyone deal with that? But at least it was a known danger. _Nice, nonthreatening kidnapper_, though? Not so much.

He cleared his throat. "What's your name?"

"Dammit, Cas, what did I _just_ tell you?"

Castiel narrowed his eyes, taking in the man's appearance. Only slightly taller than him, really…but he held himself with a sort of self-assured power that made him seem taller. Leather jacket, jeans, tee shirt, boots… "You look like a James. Or a Dean." He actually hadn't realized until he finished saying it that he was thinking of _James Dean_, and really, the man didn't look anything like James Dean, so that was stupid.

But at the second name the man choked halfway through a drink of beer, coughing violently and slamming the bottle down as he leaned over the sink.

Castiel raised an eyebrow. "Your name's Dean?" He nearly laughed, proud of himself for having gotten it out of the man, accident or not. "Well, that's something at least."

The man—Dean—gaped at him and Castiel turned his head, taking in his appearance once more. For some reason, now that he had a name, he wasn't as scary. Or maybe it was the fact that he looked like Castiel knowing _his_ name was scary. Either way, the younger man was starting to feel a bit more at ease. He pulled himself up to sit on the counter. "So then, Dean." He kept his face straight but laughed inwardly at the look of discomfort that passed over the man's face. "How much are you asking my dad for?"

Dean sighed, his head dropping as he leaned back against the counter. "A lot less than he'd probably pay—not enough to make him come after me rather than pay it."

Castiel snorted. "There's not an amount that would make him come after you. It's either an amount he'll pay, or an amount he'll tell you to kill me for."

"Come on, dude, no one's parents are that awful. He'd at least call the cops." Dean shook his head like he thought Castiel must be joking.

Of course, Castiel wasn't. And there was a small part of him that was really, really happy about the fact that this man would be irritating his father. Sure, money was his dad's preferred way to solve problems—or physically beating them into submission—but still, he'd be irritated for sure. Especially at the fact that he would have to deal with it for Castiel.

He sat up a bit as a thought occurred to him. "Hey, Dean…" He was still running through it in his mind as he started to talk. It was so simple, so obvious that he didn't know why it hadn't occurred to him sooner—why he hadn't done it _himself_ sooner. "Listen… Ask my dad for twice as much. I'll cooperate completely. Absolutely anything you tell me to do, I'll do it. Then we split it, and I take off. Let my dad think that I wasn't returned or I'm dead or…"

"Are you nuts, kid?" Dean was gaping at him, looking for all the world like he might have a heart attack. "Do you know what would happen if they thought I killed you or welched on the return? They would come after me. Right now, I'm a pretty low-level annoyance. The amounts I ask for are huge for me—_nothing_ to the people paying for them, and they always get their kids back, so I can't even guarantee that the cops have ever been involved. I know that sounds weird, but it's the only reason I can think of that I'm not on some most-wanted list right now. But if I don't return you or they think you're _dead?_ They'll come after me for sure."

Castiel's hopes plummeted as fast as they had risen. "Oh."

There was silence as Dean eyed him like he was trying to figure something out. "Why do you want your dad to think you're dead?"

Castiel shrugged. "I don't know." He did know. Of course he did. Wasn't his kidnapper's business though. "Just an idea."

Dean let out a skeptical laugh. "Yeah right. People don't just come up with ideas like that. Most are pretty much wetting themselves to go home. And I don't think it's my natural charms that've got you wanting to stay here."

Castiel was silent, unwilling to go into any detail with Dean—not even wanting to really let himself think about the details. Finally Dean shrugged and left the kitchen, pulling a cell phone out of his pocket. The action seemed to remind him, and he turned and held his empty hand out to Castiel, motioning for him to give up his phone. Except Castiel didn't own a cell phone. It was one of his dad's control issues that he had come to terms with a long time ago. All calls were made on a hard line; that way the man could track who he was in contact with, and how often.

"No way." Dean shook his head as though he couldn't believe it. "No fuckin' way a college kid in this day and age doesn't have a cell phone. Give it here." He waited, and he looked irritated when Castiel just shrugged, unable to give him something he didn't have. "Kid, don't make me search you. I'll find the goddamned phone. Just hand it over."

Castiel didn't know what to say. Getting Dean to believe that he didn't have one would involve explaining why he didn't, which would involve explaining the whole big thing with his dad—the same explanation that he had just managed to avoid minutes before.

Dean shrugged. "Fine. We'll do this the hard way."

X

Dean couldn't figure out this kid's game. One minute he was completely normal—well, weirdly normal when you considered the context of his situation, but still—and the next he was weirding out completely. First his strange suggestion (and Dean didn't know _what_ to make of that), and now this thing with the phone. He didn't get it. If the kid was going to risk harm—not that Dean had ever been completely sure he _could_ harm anyone; thankfully no one had tested him yet—then why wouldn't he have tried something in the car or the lobby? Or even the hallway outside of the apartment? Hell, he _did_ have neighbors. The walls were pretty solid, for an apartment building. He had made sure of that before he had rented the place. But it was still an _apartment_, for crying out loud.

But no. For some reason he was dead set on keeping his damned phone. Dean considered letting him. The kid didn't seem too determined to get back home. Obviously. But no, there was no way he was going down over something stupid like that. For crying out loud though, the kid was actually going to make him search him for it?

Dean shoved his hands into Cas's coat pockets, finding a set of keys—house only, no vehicle—along with a credit card and an ID. No cash. He looked closer at the ID. It wasn't even a driver's license; just a state-issued identification card like the kind the DMV gave kids who weren't old enough to drive or adults whose licenses had been suspended. The credit card wasn't actually in his name, either. It bore the name of the publishing company his father owned: Falling Grace Print.

Dean eyed the younger man's pants. "Are you really going to make me check your pants pockets?"

Cas sighed. "I don't have a phone, okay?" His tone was livid as he snatched his keys and cards back, shoving them quickly into his pockets as his face flushed red. "I can't drive, don't have a car, don't have my own bank account, and I don't have my own fucking cell phone. I'm essentially a baby in a trench coat. Happy?"

Dean was taken aback by the sudden aggression in the man's words. He raised his hands placatingly. "Okay, okay, calm down. No reason to get upset."

"No reason to get upset?" Cas's voice was becoming hysterical, vivid blue eyes flashing. "No reason to get upset? My father has essentially crippled me as an adult, I've been _kidnapped_, and then when I figure out a way that I could solve both of those problems in one swing, that doesn't work because it's not _convenient_ for the asshole who kidnapped me!"

Well. That was a lot to take in all at once. Dean stared at the shorter man in surprise. "Do you…uh…want to talk about that or whatever?" The idea of a heart-to-heart with Cas, the kidnapping victim that he had just met, made him feel itchy and uncomfortable, but the kid was clearly having some sort of breakdown.

"Do I want cheap therapy from the man holding me hostage?" Cas snapped, eyes flashing. "No." The man stormed off, leaving Dean alone in the kitchen, shocked into not following him right away.

He heard a door slam, knew from the direction that it was in that it was his bedroom door. He sighed. Well, it was probably better that he slept on the couch, anyway. Didn't need to risk Cas managing to sneak off in the middle of the night. Especially since he hadn't managed to find a suitable apartment that _didn't_ have a fire escape off the living room window. He eyed the disposable cell phone in his hand for a moment before slipping it into his pocket. He'd call Charlie in the morning. She'd drive up immediately, he knew, and it was probably best that no new factors were introduced into Cas's situation that day. Besides, it wasn't like the kid was in a hurry to get home, and Dean was a month ahead of schedule.


	3. Part Three

**Playing for Keeps**  
Annaleise Marie  
_cross-posted from livejournal  
__username: girlgotagun_

**Part Three**

X

Cas didn't venture out of Dean's bedroom until early the next morning. Dean had checked on him a few times, standing close to the door and listening, making sure that there was movement on the other side before returning to the living room. Or the fire escape. The building didn't allow smoking, and so a few times a day Dean climbed out the window onto the rickety contraption, one leg bent to brace his foot on the sill as he perched there, the other on the metal grated floor. He was more of a boredom smoker than anything. And _nothing_ was more boring than sitting alone with a hostage. Especially one like Cas, who wouldn't come out of his damned room. But Dean had no important stuff in there, no weapons, and the fire escape didn't extend to that window. So it worked. Whatever.

It was during his early-morning trip onto the fire escape that Cas finally appeared, looking half-asleep and cranky. His already-messy black hair was sticking out at odd angles, and a decent five o'clock shadow that Dean hadn't expected on the baby face had appeared.

"Bathroom?" the man grumbled when Dean stuck his head inside.

Dean shot him a confused look. "You mean to tell me that you've been in there for—" Dean looked at the clock. 7:53. "—nearly _eighteen hours_, and you haven't even come out to use the bathroom yet?"

Cas just stared at him for a moment before answering dryly. "I have considerable bladder control. Now where is it?"

Dean pointed at the door off of the living room and watched the man shuffle towards it and then disappear inside. The kid better not have been pissing in his room or something. But he really doubted that, somehow. Didn't seem like the kid's style.

"You know, man, holding it that long _really_ isn't good for you," he said when the man reappeared, looking considerably less grumpy and more awake. Honestly, Dean was a little concerned about the whole thing.

Cas sighed and flopped down on the couch by the window. "It's my dad's thing—absolute control. When I was younger, he'd lock me and my brothers in our rooms, and we could only come out when he let us. You learn to hold it, or you learn to like the smell of piss." Dean was alarmed, to say the least, and Cas took in the expression on his face before shrugging. "Not the worst he ever did."

Dean coughed uncomfortably. "I thought you didn't want to talk about it?"

Cas shrugged. "Changed my mind. I figure, who are you gonna tell? Like you're gonna go out with your friends and tell them, 'Oh, I kidnapped Castiel Novak the other day and you'll never guess what he told me'?" Cas's eyes flicked to Dean's, narrowed in suspicion. "I mean, I'm assuming your friends aren't in on this."

"Don't have many friends." Dean noticed his cigarette burning down to the filter, forgotten as Cas had been speaking, and ducked back out to the fire escape. He jerked his head for the man to follow, surprised when he clamored onto the fire escape a moment later. He hadn't really expected him to do it. "But yeah, my closest friend, Charlie…she's in on it."

Cas laughed. "What, are you Bonnie and Clyde or something?"

"Nothing that crazy." But that was all Dean offered. He shouldn't have even let Charlie's name pass his lips. He hadn't called her yet, and he was beginning to consider not doing so, with how badly this job had been botched. And now, if Cas _did_ decide to try to press charges—he could certainly identify him accurately at this point—he had implicated Charlie as well. Awesome. "So your dad…just how completely nutty is he?"

Cas shrugged. "Never had anything to compare him to, really. He's not normal, that's for sure. My older brother Michael, though… He swears it's not that bad; that Dad's just a bit unconventional, but that he's raised us strong."

"I don't think keeping you financially dependent and making you hold your piss for the better part of a day does more for your strength of character."

"Probably not," Cas agreed easily. "I'm beginning to think most of the Novak men are a bit off, honestly."

"Well, you don't seem much like them."

Cas didn't answer him right away, fixing those unnervingly blue eyes on Dean for a few moments as though trying to figure something out. "Maybe not. Maybe I'm just an entirely different kind of crazy."

Dean laughed. "Well, you _are_ kind of just making idle conversation with your kidnapper."

"Man, this is the first time this summer I haven't woken up in my dad's house, wishing I hadn't." Cas shook his head. "Sad to say, it's a marked improvement."

The thought made Dean a little sad.

X

The day slipped by, and still Dean didn't call Charlie. Didn't call and make the ransom demand. He figured after what he was putting the kid through, the least he could do was give the poor guy a day out from under his dad. He checked the news in the morning, at noon, and again at seven. There were no reports of Cas missing. And that didn't strike Dean as particularly odd, given what Cas had told him about the man, other than the fact that the man was obviously a control freak—he _was_ surprised that he would let Cas out from under his thumb that long.

Maybe he had written Cas off as a runaway; didn't care enough to check up. Maybe there was a hold up in reporting because Cas was an adult. Dean thought he had heard something about there being a requisite forty-eight hours before an adult could be reported missing. But he wasn't sure if stuff like that applied to people with Cas's father's power and wealth.

He decided he'd wait another day or two and see. It was a risky gamble—if the man was only waiting out a forty-eight hour mandated period, then Dean was guaranteeing police involvement. But he couldn't help it. For some reason, he really, really wanted to know.

In the meantime, he and Cas lived in uneasy sometimes-silence. Occasionally Cas would ask questions about him, which Dean would answer vaguely. He felt bad that Cas had been so open with him, but he was holding so much back. But then, Cas wasn't the one risking prison time if he told too much.

At the end of the second day, Cas finally asked him.

"Has my dad responded to the ransom demand?" He didn't look at Dean as he said this. They were out on the fire escape again, and Dean whipped his head around quickly, checking for open window and others out on the fire escape. Thankfully, they seemed to be alone and out of earshot of anyone who might be nearby.

Dean shook his head. He didn't tell Cas that he hadn't made the demand yet. Didn't tell him that he was waiting, testing out Cas's claims of how horrible his father was. Didn't tell him of the building hesitance he was feeling when he thought about sending the younger man back to that.

Cas sighed, sliding down the metal rail support to sit on the grate. "Sorry he's being an ass. I'm sure you don't want to be stuck with me any longer than you have to."

Dean scoffed. "What's gotten into you?" The younger man was weird, that was for sure, but all that day he had been pretty…normal. Not this self-depreciating, mopey persona that had suddenly come out.

"I think a lot of the stuff that my dad did…sort of socially crippled me. I almost forgot that we're not friends; that I'm just a job to you. And I'm sure you're not thrilled about it taking this long." Cas was looking out over the city through the railing supports, not turning towards Dean as he spoke, as though embarrassed by his behavior.

Dean shifted uncomfortably. He wanted to tell the other man that that wasn't it; that he hadn't even made the demand yet, and that of course Dean didn't mind him talking to him, that he even sort of liked it. Instead he said, "I don't have anywhere else to be, really."

Cas turned to him then, his expression unreadable. "It must be like being stuck at work every second of the day."

Dean shrugged. "I work in an auto shop with two grumpy old men. This is like a vacation." He nearly bit his own tongue trying to stop the words from spilling out. Dammit, he needed to stop telling Cas things about himself.

Fuck it, he thought grumpily. If Cas was going to turn him in when this was all over, he had plenty information to do so already. Dean's ass was pretty solidly in the fire. No point trying to be careful now.

"You mean you have an actual day job?" Cas looked genuinely shocked. "Then why the hell are you doing _this?_"

Dean laughed and tossed his cigarette butt off the fire escape without thinking about it; he wasn't used to being on the eighth floor of a building. "I know you grew up in the lap of luxury, Cas, but nine-to-five labor jobs at little family businesses—they don't pay well. And college is expensive. Especially Stanford Law."

Cas looked even more surprised, and for a minute Dean couldn't figure out why. Then it hit him, and he wanted to hurl himself off of the fire escape. Well, that was the last of it. He had now thrown Sammy into the mix.

"You're in school? To be a _lawyer?_" Cas looked like this was extremely funny, and Dean supposed that, looking at it like that, it sort of was.

He shook his head. "My brother. He's crazy smart; driven… Never wanted the life that our dad wanted for him. He wants to finish school, settle down, have kids and all that, and work at saving the world at his nine-to-five."

Cas was quiet for a moment as he took this in. "You're doing all of this…for your brother?"

Dean shrugged. It wasn't like it was a completely selfless act. He and Charlie benefitted, after all. If it were strictly for Sammy, the first job would've been enough.

"That's actually very…sweet, Dean." Cas was smiling at him, the expression so freaking genuine and admiring that it made Dean's gut twist with guilt.

"Dude, I _kidnap people_. Trust me, there's no _sweet_ way to look at that."

Cas was quiet again, this time looking as though he were trying to work out how to phrase something. After a moment he sighed. "I guess I've just never known of anyone who would go to such lengths for someone else. Everyone in my life is constantly trying to put themselves ahead; do what's most beneficial to them." He smiled again, but this time it was half-assed, not reaching his eyes. "I sort of wish someone had ever cared about me like that."

"Enough to kidnap someone for you?" Dean laughed. The sad look didn't leave Cas's eyes as the younger man shrugged amicably, and it stopped Dean's laughter immediately. "What if I cared enough to not give you back?" Dean didn't know what made him say it, what he was even thinking of when he said it. But it rang strangely true in his own ears—he didn't want to send the kid back to his dad, to that life that brought so much sadness and pain into those bright blue eyes.

Cas's smile got a little warmer. "I'd like nothing more than to never go back."

Dean didn't answer him, and Cas didn't ask anymore questions. After awhile they went back inside, and despite the part of his mind that was still on the job raging at him, Dean didn't object when Cas sat close to him on the couch as they watched the ten o'clock news.

There was still no report that Cas was missing. Dean looked at the clock. It had been fifty-seven hours since Cas had gotten in his car.


	4. Part Four

**Playing for Keeps**  
Annaleise Marie  
_cross-posted from livejournal  
__username: girlgotagun_

**Part Four**

X

Dean woke up on the morning of the third day sandwiched between the back of the couch and a warm body. He remembered falling asleep half stretched out, his legs extended in front of the couch. Cas had been seated on the middle cushion. Whether they had moved to lay down completely before actually falling asleep, or whether they had moved in their sleep, he wasn't sure. But the fact remained that Dean was now stretched out, spooning with his hostage. And to make it worse, he had raging morning wood. Of course he did. Because next to the time that he had woken up after he and Charlie had passed out completely blitzed on her bed, this was probably the most inappropriate time to be hard.

He moved slowly, planning on figuring out how to somehow get out from behind Cas without waking him up. But even the slight movement of the couch that resulted from him trying to sit up was enough to make the younger man stir, a small sigh escaping his lips as he scooted closer to Dean, effectively rubbing his ass against Dean's dick, which twitched interestedly at the contact. Dean gritted his teeth as he worked to keep himself from rutting into the warmth. It hit him, suddenly, just how long it had been since he had actually gotten laid. In abject defiance towards Sam's attempts at setting him up, he hadn't slept with any of the women his brother got him to go out with—didn't want to give them (or Sam) the idea that he was interested. Add to that his time at the garage, planning this job, and a huge chunk of his time being spent with Charlie—a lesbian—and it all added up to about six months without any action whatsoever.

He decided that subtlety wasn't going to do it—he had only managed to get himself pinned tighter behind Cas with that approach—and put his hands on the smaller man's shoulders, holding him in place as he quickly sat up and climbed over him. He heard the man mutter something as he woke up, sounding pretty disoriented at Dean using him as a springboard, but before he could really form a sentence Dean was safely in the bathroom, the door shut and locked behind him.

He sighed in relief, leaning back against the door. That had been close. Hopefully Cas hadn't noticed anything. He looked down, frowning at the obvious tent in his pajama pants. He was twenty-six. Well past the age of waking up _every morning_ with a raging hard-on; but of course his traitor dick had decided that this morning was the perfect time to get all nostalgic about those days.

He grudgingly turned on the shower, figuring he'd just take care of it in there; make the most of the time, since no matter how cooperative of a kidnapping victim Cas had been so far, he knew it wouldn't be smart to leave the man alone too long. The thought of Cas brought the memory of his ass pressing into Dean back to the surface of his mind and he beat it down forcibly. It wasn't actually that Dean had a problem with fucking guys—far from it, really; sex was sex. But Cas was, again, his _kidnapping victim_. He couldn't let himself forget that. He was absolutely sure, even if Cas was one hundred percent on-board with the idea of Dean fucking him, that any court in the country would tack that on as sexual assault if he went down for this botched job.

Still, when he stepped into the shower and braced his hand against the wall, letting the other wrap around his hard cock, he didn't fight too hard to control whether or not it was Cas that he imagined touching him. And of course it was. The man's proximity alone and the sense memory of his warmth against Dean as he slept was enough to ensure that would be the case. He couldn't be tried for the things he did in his mind, so he went with it. As he jerked himself off quickly, his mind put Cas through the paces—on his knees, those pouty lips stretched wide around Dean's cock as the younger man fisted the part he couldn't fit in his mouth; leaning against the wall, ass jutted out as Dean fucked into him ruthlessly, biting his lip to keep from screaming as his inner muscles milked the older man's cock; his legs wrapped around Dean's waist as Dean pressed him into the shower wall, his head thrown back as he screamed Dean's name, urging him to thrust into him faster, harder…

He came hard, stifling a loud groan that may or may not have contained the younger man's name against his shoulder as he splattered the tile, his chest heaving as he came back down from the high, knees weak. He quickly washed off, not wanting to draw any questions from Cas regarding the amount of time it took him to shower.

When he came out of the bathroom Cas was waiting for his turn, leaning against the wall. Dean felt himself flush, hoped the younger man didn't notice.

He didn't notice the small smile on Cas's face as he ducked into the bathroom.

X

Dean's phone rang around noon. He and Cas were waiting for the news to come on—Dean hadn't told Cas _why_; the younger man probably figured that he had some weird obsession with current local events—and Cas sat up, his eyes wide as he stared at Dean. The freaked-out look on the kid's face confused the older man for a moment, and then he realized that he probably thought it was a call about the ransom. Dean shook his head. The caller ID told him that it was Charlie, and he hesitated before answering it.

He did, though, catching it right before the ringtone played out. "Hey."

"Hey so listen; I've been thinking about this and I'm not so sure if this is a good idea. It's definitely going to be a lot harder pulling off a job with an adult and he's _way_ more likely to pay attention so that he can identify you later. Plus, I've been finding my way into up all this stuff on Novak and I don't think he's the kind of guy we want to fuck with."

Dean swallowed, his eyes flitting to Cas. "Oh yeah?"

"Yeah. Apparently he had a younger son; Castiel wasn't always the last in the line. His name was Gabriel and apparently he drown in their pool when he was seven but it's weird, because when I dug deeper, the FBI was _all over it_ when it first happened. The report that he drowned wasn't the original autopsy, either. The original one cited that a cause of death couldn't be confirmed _although there was water present in the lungs consistent with drowning_." She sounded like she was reading the last part out loud. "Seriously, Dean, I'm getting the creepy-vibes off of this guy."

"Yeah. Yeah, me too." Dean stood up, suddenly full of nervous energy. "Listen, can I call you back?"

"What? Why? I really think we need to figure out what we're—"

"Bye, Charlie." Dean hung up the phone. Panic was seeping deep into his bones and he could feel Cas's confused stare on his back. He threw open the window and climbed out onto the fire escape, needing fresh air, needing to be out of the suddenly-tiny apartment. His hands fumbled with this cigarettes and lighter, out of nervous habit associated with being on the fire escape, and once he had one lit he leaned over the edge of the railing, trying to will his nerves to calm down.

"Dean?" Cas's voice was close behind him; the younger man had followed him onto the platform. He sounded concerned, _way_ more concerned than he should have when talking to his kidnapper.

Dean wanted to laugh hysterically, felt it bubbling up in his chest, barely able to contain it. Of course Cas was concerned about him. Of course it didn't matter that Dean was a monster who kidnapped him. Because Cas had been raised to love a monster who had killed one of his children and abused the rest. Compared to that, Dean was fucking Mary Poppins.

"Cas…" Dean began, turning to look at the man once he was sure he wasn't going to break down in hysterics. "What happened to Gabriel?"

The light disappeared in Cas's eyes. It was like the younger man shut down completely, his face impassive, posture slack. And Dean knew, even before the younger man turned and went back inside, even before he heard the distant slam of his bedroom door, that he wasn't going to answer.

X

Cas didn't reappear until late that night. Dean had finished watching the ten o'clock news—eighty-two hours since Cas had gotten in his car and still nothing—and he was stretched out on the couch, eyes drooping with fatigue but mind unable to stop spinning long enough to let him fall asleep. Cas reappeared, little by little, and Dean didn't move, didn't want to scare the other man off as he tracked his movements in the shadows of first the hall, then the doorway, and then the edge of the room.

When Cas moved to sit on the couch, Dean moved his legs to let the man curl up against the arm. The older man waited, his eyes watching Cas carefully—Cas's eyes dull and out of focus as he stared at the infomercial that was slotted to follow the new.

_It chops! It dices! It blends! Just one Ninja can replace all five of these household appliances, saving you from dealing with the aggravating clutter!_

"Gabriel was a warning." Cas's words were sudden, sharply-spoken, his voice bitter and low. "He was a sweet kid; liked to joke around a lot, ate candy like it was the only food on the planet. He wasn't really supposed to—our dad was really strict about what we ate. But we'd all sneak Gabriel candy. Because he was the baby, and it made him happy. Even Michael." He paused, his eyes narrowed. "I think Michael would kill me or Raphael or Luc if our dad told him to. Definitely Luc. But even he had a soft spot for Gabe. Spoiled him rotten."

Dean nodded. He could feel the younger man's body trembling where his leg was touching his hip, could hear it in his voice. He wanted to sit up, to pull Cas close to him and try to comfort him as he told the story. But he was afraid that doing so would scare him, would make him retreat again.

"Gabe didn't even really do anything wrong. It wasn't about him; it was about us. I was starting high school. Luc and Michael were in college, and Raphael was a senior. I think our dad started to worry that one of us would rebel, would challenge him, finally decide we had had enough. And I guess he was right, cause Luc walked away a few years ago and never looked back." Cas shook his head. "But I think he was trying to scare us, you know? Keep us in line. So he brought us outside one night, told us to never forget what would happen if we decided to go against him. And then…he showed us what would happen." His voice was getting thick, his eyes watering. "He held Gabe underwater, held him and made us watch until Gabe stopped fighting. Until he couldn't fight. And we… I just watched. I was too scared, couldn't move. I was too scared that he would kill me to try to save Gabe."

And then Dean did sit up, did draw the man towards him as he shattered completely, shoulders heaving as he cried.

He didn't fight Dean, just kept talking as though he couldn't stop now that he had started. "He had…these s-scratches…all up and down his arms…for w-weeks. And the police saw. Saw and d-didn't say anything. They s-said that Gabe d-drowned. That it w-w-was and _accident_." The last word was hissed with venom, drawing a fresh wave of hot tears from the man. They dripped onto Dean's forearm where it was circled around the man's chest.

Dean closed his eyes, tried to calm his own anger at the story. It wouldn't help Cas any for him to get angry—might even scare the man. So he stayed quiet, stayed calm—or at least made it a point to seem like it—and held the other man tight, enveloping him with his own body to hold him together as he fell apart.

X

Dean lost track of how long they had laid there like that; how long Cas had sobbed or how long it was after he stopped that he fell asleep. He wasn't sure exactly when his right leg had fallen asleep, but he was trying not to move it, not to wake Cas. His mind was still spinning over the story that the man had told him.

There was no way that he could send Cas back to that. No way in hell. Four brothers had stood in a row as their father murdered the fifth, and they had all been too terrified to do anything to stop it; too terrified to speak up later. And Dean didn't blame Cas or his brothers for any of that. But it meant that if he sent Cas back, and something happened to him, that no one was going to step in to stop it, or speak for him after the fact. And Dean couldn't handle that thought, couldn't deal with the idea of Cas fighting as his dad held him under…until he stopped fighting.

He just couldn't figure out how to handle _not_ sending him back, either. There was no guarantee, if the eldest Novak was that kind of man, that he didn't have privately hired guys on Dean's trail right now. It would explain the lack of police involvement even after so much time. So even if he and Cas ran away—and that was _if_ Cas would even want to stay with him—there was no guarantee that someone wouldn't find them eventually, that Novak wouldn't still get hold of his youngest (surviving) son.

The idea hit him just before sunrise, and he gently untangled himself from around Cas, laying the man back gently on the couch. He went to his room and found Cas's coat on the hook by the closet, the Fallen Grace Print credit card still in the pocket. He was willing to bet that the card didn't have ATM privileges—that would grant Cas access to too much resources without a paper trail on what they were being used for—but luckily no such restriction had ever stopped Charlie.

He called her, using up every last favor he had wracked up in their decade-long friendship, and finally convinced her to stop asking questions and crack the damned card. When all was said and done, she pulled nearly three million dollars from it before the fraud protection algorithms got too complex and locked her out effectively. It made Dean's head spin. He had never considered that kind of money being at their disposal. But it wasn't, really.

It was for Cas.

"You want me to filter it into the normal accounts?" Charlie asked, sounding nearly as awed as Dean felt.

Dean shook his head despite the fact that she couldn't see him. "No. Set up a new one. Dump it in there."

"What name?"

Dean paused, his mind racing. "Cas Winchester."

There was a pause, and then Charlie exploded. "_Are you fucking kidding me?_"

X

Dean spent the rest of the night packing. He hadn't brought much with him for his planned six-week-max stay at the apartment, but he kept making nervous circuits around the house, the feeling that he had forgotten something eating at him.

It was a few hours before he realized what was causing the feeling.

It was Cas. He felt like he was forgetting something because he didn't know yet if he was taking the man with him, or parting ways with him in the morning.

The latter thought was like a knife through his heart.

X

The sun had risen completely, making Dean blink in the glare on the fire escape. The sounds of Cas stirring inside jarred his nerves, and he took another long drag off of his cigarette. Eight crushed filters were lined up at the bottom of the rail. He hadn't smoked this much…ever. He'd never had his nerves this much on edge.

He heard the younger man clammer onto the fire escape after a few minutes, looking disoriented in the bright light. His eyes landed on Dean's, and he shifted nervously.

"I'm sorry for breaking down like that." His voice was low, embarrassed. "I'm sure that was awkward. When I started to tell you the story, I thought I would be able to do it without getting so emotional."

Dean furrowed his brow, confused by Cas apologizing for being upset about the death of his baby brother. If it had been Sammy… Well, Dean couldn't even begin to imagine what he would have done if it had been Sammy.

"Has my father called?"

Dean tossed the cigarette in his hand, cringing as it sailed down. It was a good thing they weren't staying—regardless of what circumstances they left under—because he was going to burn someone in the alley one day. "I never called him."

"What?" Cas sounded confused.

"I never called him. At first I figured that you could use a day or two away, even if it wasn't a great situation, cause of how weird you acted about going back. And then all this stuff about your dad started coming out and then last night…" He swallowed, bracing himself for the next part, for any myriad of reactions from the younger man. "Last night I decided I'm _not_ taking you back. Charlie pulled as much as she could off of your corporate card and buried the trail so that it couldn't be traced. Nearly three million dollars. I don't know what kind of money that is to someone like you, but trust me, you can do pretty well with it on your own. I had her put it in a bogus account."

Cas seemed to be taking a moment to absorb this information. "On my own?" he repeated finally.

Dean nodded. "I…I want you to go with me. We can get a place, live off of your dad's radar. I'll do whatever it takes to keep him from finding you; whatever it takes to keep you safe. But you don't have to. You're not my hostage anymore. You can…"

Dean didn't get to finish his sentence before Cas's lips were on his.


	5. Part Five

**Playing for Keeps**  
Annaleise Marie  
_cross-posted from livejournal  
__username: girlgotagun_

**Part Five**

X

It took Dean a moment to process what was happening. Cas's lips were soft and warm on his own, and he had barely begun to react before it was over, Cas pulling away.

Bright blue eyes stared into his, alight in a way that Dean hadn't yet seen. "I want to go with you." It was quiet, nearly a whisper, but with the strength and conviction of a sacred oath.

And then this time Dean was kissing Cas, his hands coming up to hold the younger man's face still as he tried to put everything that he was feeling—relief, anxiety, lust…love?...if not love, something close, _almost_—into the kiss. Cas's hands came up to grip his shoulder's, the shorter man standing on tiptoe to try to gain control of the kiss. Dean pulled away, his breathing heavy, mind racing.

"Inside." His voice was low, raspy with need. He meant it to be a question, a suggestion, meant for it to have an implication of _if you want to_, but he was rapidly sinking too far into want, need for the younger man.

But Cas didn't seem offended. He nodded and turned, ducking back through the window with Dean close behind him. They barely had their feet on the floor before they were locked at the lips again, neither of them sure this time who had initiated it, parting only to discard their clothing on the way to the bedroom before they fell to the bed, naked. Dean moved Cas easily onto his back, his lips traveling over the stubble-covered jawline and pausing to nibble on his ear, drawing a moan from the younger man before continuing on, trailing his lips down his neck, sucking lightly at the spot where his neck and shoulder met and then trailing his tongue over the man's collar.

He smiled against the soft skin when Cas arched into his touch. The smaller man was so fucking responsive, so sensitive to every little touch, and Dean felt his own body respond, his cock growing impossibly harder as it gave a needy throb. He ran his tongue over a dusky pink nipple, sucking on it lightly and then biting down just hard enough to make Cas gasp before he soothed the pebbled flesh with his tongue. He gave the same treatment to the other one, moaning when he felt Cas arch against him, the other man's hard flesh sliding against his ribs, seeking friction.

"Dean, please, I need you…" The younger man's voice was small, vulnerable.

And normally Dean would ask what he needed, make him tell him exactly what he wanted him to do; but this was Cas. And Dean wasn't there to play games with Cas—he wanted to pleasure him, shatter him in the best possible way and then piece him back together. Heal him.

He moved down, raining soft, open-mouthed kisses onto every inch of smooth, pale skin along the way, dipping his tongue into the younger man's navel, nuzzling at the light trail of hair that started just below it, leading down to what Dean thought—although he was probably biased—was the most beautiful cock he had ever seen. And it was a funny thought, but he didn't laugh as Cas arched again, begging Dean with a light whimper.

He brought his mouth to the hard shaft, running his lips along it from the base to the head before placing another light kiss there, reveling in the breathy moan it drew from the other man before he took the head in his mouth and sucked lightly, his tongue swirling over the slit to taste the bead of precum that had formed there. He hollowed his cheeks, sucking lightly as he slid his head down, stopping when he felt the head nudge the back of his throat. He had never been one for giving head, really; never saw the appeal. But the cry it pulled from Cas's lips as his hand came down to grip Dean's shoulder, the other twisting into the pillow under him…yeah, that was definitely worth it.

He wrapped his hand around the part of the shaft that he couldn't easily fit in his mouth and started a slow, steady pace, drawing back to the tip, swirling his tongue over it and along the ridge of the head before sucking back down. It wasn't long before Cas was moaning, trying to thrust up, and Dean moved to lick at his balls, chuckling at the needy whine that issued from the younger man.

He spread Cas's legs wider, settling between them as the younger man blushed, apparently embarrassed at being so open and on display. Dean leaned down, kissed him softly. "So fucking beautiful, Cas." He muttered the words against the other man's lips, whispered it like it was a solemn secret they shared. "So perfect."

He ran a finger along the crease of the man's ass, dipping between the cheeks to softly rub against the puckered opening. He nearly groaned when he realized he didn't have lube, wracking his mind for anything that he could use in its place. He didn't want to hurt Cas—never wanted to hurt him—but he hadn't exactly planned on this job turning into sex, either, and he was pretty ill-prepared. And then he remembered that Charlie had borrowed his bag a few weeks before he had left for Seattle, and she had left a bottle of lotion in the side pocket. He almost wanted to call her and thank her for being so gloriously absent-minded.

He leaned over the bed, digging around in the pocket of the bag for a moment before he finally found the small bottle. Cas looked confused at first, and then understanding washed over his face and he laid back again, his eyes soft and trusting.

"Cas, are you sure you want to—" Dean started to ask. He felt like it was only right. He had no idea if Cas had ever done this before, didn't want to pressure him into it.

"Please, Dean." The man smiled. "I want to do this with you; want to be yours." He laughed. "I mean, went through all the trouble of abducting me. You may as well enjoy it."

Dean frowned. "It's not like that, Cas."

The smile disappeared from the other man's face and he sat up. "Sorry. I know it's not. I'm just…nervous, I guess. I was trying to make a joke." He kissed Dean softly. "But yes, I want this very much. Want _you_."

He laid back, spreading his legs invitingly, and Dean nearly moaned at the wanton move. He needed to be inside the man, and soon. If he waited much longer, he wouldn't last once they were finally there.

It took everything in him not to rush preparing the other man, to make sure that Cas had adjusted completely to each finger before he added another. He sought out his prostate, grazing it teasingly, his cock twitching when Cas cried out and started to rock down onto his fingers, seeking out more.

Finally Cas told him he was ready, told him to do it, and Dean lined himself up, pausing before pushing in to press his lips to Cas's once more, kissing him as he slid into the tight, warm heat. He had never felt anything like it. Sure, sex was sex, but this with Cas couldn't really be reduced to something as simple as _sex_. He felt complete, connected to the man on a different level as he drank in every sigh and every moan and cry of pleasure.

"God, Cas, you feel so good," he muttered, his lips finding every inch of skin they could at each pause in the words, his hips thrusting at a pace that was driving them both quickly to the edge. "So fucking good. Always gonna make you feel like this; never let anything bad happen to you." He breathing was coming in sharper gasps now, Cas's moans becoming louder as Dean brought a hand between them, stroking the other man in time with his thrusts. "Fucking love you."

And with those words, those three words that Dean didn't even realize that he said out loud, Cas screamed his name, his muscles fluttering around Dean's cock as he climaxed, his cum painting both of their stomachs and chests as his cock twitched in Dean's hand.

Dean swore loudly, burying his face in the younger man's neck as he felt himself go hurtling over the edge, shooting his load deep inside of Cas, his hips thrusting lazily to draw out the last of the orgasm as he trembled on top of the other man.

"Love you too, Dean."

And that was when it hit him, what he had blurted out in the heat of the moment. And for a moment, he was embarrassed. But only for a moment. Because hell, it was true. And Cas felt the same. And that was all Dean could ask for.

They would lay there for awhile, recover their senses, and then they would clean up and head to the car, leave Seattle forever. They'd head for Palo Alto, and from there…well, they'd figure it out as they went. As long as they went together.

**The End.  
**_I hope you enjoyed it. :)_


	6. Expansion Announcement

**Announcement!**

Hey guys! First, let me say how amazing the response to this story has been between the three sites it's been hosted on has been. I never expected this little fill to take off the way it did!

I've received a lot of questions about what happens _after_ the story ends, but also about more detail in a few things in the story.

I'm pleased to announce that I'll be exploring all of those questions-and more-in a revamp/expansion of this fill, a full-length story titled "Under the Gun". The first chapter is up now, so check it out if you're interested!

Love,  
Anna.


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